The Top 10 Things I Have Learnt On My Travels From The Last 15 Years…So Far

The Top Things I Have Learnt On My Travels From The Last 15 Years…So Far

After 15 years on the road and over 75 countries explored, I’ve had my fair share of missed buses, border mishaps, budget wins, breathtaking hikes, and unforgettable friendships. In this solo episode of the Winging It Travel Podcast, I share the top 10 lessons I’ve learned from traveling the world — insights that can help you make your adventures smoother, deeper, and more meaningful.

From the importance of packing light and learning a few phrases in the local language, to why slow travel beats rushing through bucket lists, I dive into the hard-earned lessons that only come from years of backpacking, volunteering, and chasing stories across the globe. You’ll also hear why free walking tours are a goldmine for cultural connections, why the off-season is the best time to travel, and how nature is the real luxury we often overlook.

🌍 In this episode, you’ll learn:

  • How to expect the unexpected and adapt when things go wrong.
  • Why travel friendships are so unique and unforgettable.
  • The resilience and creativity that budget travel teaches.
  • How choosing off-season travel benefits both you and the locals.
  • Why the world is a much kinder place than the media often shows.

Whether you’re a seasoned backpacker, a gap-year adventurer, or planning your very first trip, these lessons will inspire you to travel with more confidence, awareness, and curiosity.

🎧 Tune in now to hear the raw, real, and reflective side of travel — because these aren’t just stories, they’re tools to help you travel smarter, deeper, and more authentically.

💬 What about you?

I’d love to hear the biggest lessons you have learned on your travels. Share your thoughts with me on Instagram @wingingitravelpodcast or drop me a DM — I might even read out your stories on a future episode!

⭐ Support the Podcast

If you enjoyed this episode, please rate, review, and follow the Winging It Travel Podcast on your favourite podcast app. Every 5-star review helps more travellers like you discover the show. Even better, tell your friends to check out the many different types of episodes, such as this raw solo episode, my immersive cinematic experience episodes from my travels, or the incredible guests I have had on the podcast to date.

🔗 Connect & Explore More

🚀 New episodes drop every Monday — so subscribe and join me on this journey of real, raw, and inspiring travel stories from around the globe.

Timestamps

00:00 Introduction to Travel Lessons

02:14 Expect the Unexpected

05:26 Connecting with Local Culture

06:53 The Benefits of Light Packing

07:52 Learning Local Languages

10:20 Travelling Off-Season

12:38 The Luxury of Nature

13:34 The Uniqueness of Travel Friendships

16:31 Resilience Through Budget Travel

18:23 The Value of Slow Travel

20:16 The Kindness of the World

————————————————————–

Voyascape: Travel Podcast Network – https://voyascape.com/

Winging It Travel Podcast – Website

Please leave a review and a 5-star rating wherever you get your podcasts!

————————————————————–

Winging It Travel Podcast Credits

Host/Producer/Creator/Composer/Editor – James Hammond

Contact me – jameshammondtravel@gmail.com 

Social Media – follow me on:

Instagram

TikTok 

Facebook 

————————————————————–

Support My Podcast – Memberships

Patreon – Here

Buy Me A Coffee – Here

Affiliate Links 

If you click one of the below to book something, I get a tiny commission, which helps the podcast.

Book Flights with Skyscanner – Here 

Use Revolut Travel Card – Here

Book Your E-Sim With GigSky – Here

Book Hostels With Hostelworld – Here

Booking.com – Here

Book Experiences With Viator – Here

Discovery Car Hire – Here

Book Buses With Busbud – Here

Book Trains With Trainline – Here

Travel Insurance with SafetyWing – Here

Book Flights With Expedia Canada – Here

Buy my Digital Travel Planner – Here

————————————————————–

Thanks for supporting me and the podcast!

Cheers, James.

Transcript
James Hammond (:

Hello and welcome to this week's solo episode. This is 10 things I've learned on my travels and they're kind of divided into two parts. One part is things I've learned about people, about culture whilst traveling. The second part is about the way we should travel in terms of what I've learned on my travels. So in the future, I've taken some lessons I've learned in terms of the best way to travel that I think will enhance my travels and maybe even your travels. So I've got two types of things going here.

Lessons learnt from me, but lessons learnt about how to travel. So I hope you enjoyed the top 10 things. Let me know what yours are in the comments on the podcast episode, or you can DM me or message me on Instagram. I'll see you at the next episode. Let's get stuck in. Welcome to the Winging It Travel Podcast, your weekly ticket to the world, dropping every Monday and hosted by me, James Hammond, proudly part of the Boy Escape Network. This is a travel podcast that throws out the itinerary and dive straight into the raw

real and unpredictable essence of global exploration, chasing moments over milestones, those spontaneous encounters, immersive sounds and unforgettable stories. Whether I'm hiking up volcanoes in Guatemala,

James Hammond (:

or camping under the stars in British Columbia.

met incredible people, seen breath taking places and collected unforgettable stories. I now get to share them with you, alongside some of the most diverse and well travelled guests from around the world. Expect engaging conversations that bring fresh perspectives and inspiring travel tales. There are also raw, reflective, subtle episodes where I share personal insights, practical tips and honest stories from the road. This is a podcast for travellers, dreamers, backpackers and anyone who's ever thought, what if I just went for it and travelled. If you're looking for stories to tell, tips to share,

and experiences to inspire, then you're in the right place. There's so much travel content coming your way, it might just spark that trip you've been dreaming about for years. You can find Winging It, a more fantastic travel podcast from around the world at voyescape.com. The link is in the show notes. Let's go and explore the world. I'm Hammo and I've traveled to around 75 countries in last 15 years.

and I've slept on beaches, in train stations, I've missed buses and flights, I've eaten some questionable street food, but every single one of those has taught me something on the road. And some of these are life changing, some of these are funny, and some of these are just damn right common sense. So let's get stuck in to the top 10. Let's go. Number one, always expect the unexpected. I think key to travel is being adaptable to any situation you might find yourself in. The best stories normally happen when things don't go according to plan.

or had to change plans for your travels. Now for me, I've been adaptable in many situations.

James Hammond (:

So when I was in Laos crossing over to Thailand I got held at the border for unknown reasons at the time. Couldn't work out why they're shouting at me. I really don't know what to do. I ignored them, went on the boat across the river to Thailand. was heading back across the river on the boat and there were four guys waiting for me at gunpoint to take me to a post by the border and I had no idea what to do. But luckily just before that my friends who did get through the border okay gave me some US dollars. I had some Thai Baht and I had my

negotiation skills on the go. Fast forward. I've actually forgotten to get a stamp into the country. I must've missed a sign. Wasn't that obvious? It was a genuine mistake. But in this 30 minutes, there was to and fro between me and them. Language barriers, money been negotiated, snooker on the TV. Ron O'Sullivan was playing snooker. It was a stranger situation and no one was budging. I was pretty annoyed, pretty stubborn, but I realized pretty quickly if I'm going to get out of here and get my bus to Chiang Mai.

. Back in those days in:

30 minutes of talking, silence, trying to gauge each other. Pretty scary environment. One of those had a gun and yeah, learned a lot from that lesson in terms of you got to be aware of situations when crossing land borders that could affect your trip. And that was one of them. So the key lessons I learned on this situation amongst many others like missing buses in Vietnam, trains getting delayed in Malaysia, my friend nearly falling off a cliff on Death Road in Bolivia is that you need patience.

Trust in the process, be willing to make tough decisions under tough conditions in a short timeframe. I tell you what does help and is underrated is knowing a little bit of the language, but I'll come to that later in the episode. Let's go to number two. Number two is free walking tours are the best way to connect with local people and culture. I am a huge fan of free walking tours everywhere I go in the world.

James Hammond (:

Every place I visit that I'm there for a day or two, I book in a free walking tour. I actually use the free walking tour guides as a potential guest on my Willing It Travel podcast because they come on, they can speak decent English and are willing to share their city or their place and also what they offer in terms of a guide. These guys will speak English to the group. They'll have so much more knowledge than you'll ever have of that place. They'll be nice, welcoming. You can ask as many questions as you want. But most important thing of all, when you're finished with your tour,

make sure you tip the guide. To finish on this lesson, in that walking tour group, there may be travelers that you may meet for the first time and hang around for a few days and they may become lifelong friends. But again, another point I'll come to in a bit. Let's go to number three. A light pack beats a heavy pack. I am one of those people that will take just a backpack and carry on only. It's controversial. I understand a lot of people want to carry a suitcase, but for me,

get the most out of my trip to save on fees, but also to be bit more mobile, I only take carry-on at the most. I have an Osprey 40 litre bag, which is roughly around 10 to 12 kilos. The dimensions are just enough to fit onto carry-on, so it's allowed on on most flights, I must say. It doesn't quite fit in the overhead compartments of Ryanair, for example, but on big flights, carry-on only. And for me, that is an adaptable backpack. That could be a day pack as well. I could even stuff one on top of that or in it.

And also for a carry on, it can fit a lot of stuff in. Now for me as a creator, the big thing has changed recently from previous years is tech, laptops, microphones, cameras, phones, whatever I need to create this YouTube channel, but also my Winging It Travel podcast. Light packing also saves a little bit of stress. Hear me out on this. You've got a big suitcase, you've got a big backpack. What happens if he needs something really quickly, but you've packed it in that big pack? Where is it?

It might be right down deep in the pack. got to shove everything out, move things to the side, annoy people around you. You're getting stressed. They're getting stressed. It's not a nice situation, but a smaller backpack, more controllable, more little compartments you can label. It's just easier to travel as a light backpacker, but I get it. It's not for everyone, but that's my lesson I've learned for number three. Number four, learning a few local phrases in the local language. I cannot emphasize how important this is. This is

James Hammond (:

arguably the biggest lesson I've on this list because instantly you learn 10 words. Hello, please. Thank you. How are you? What's the response to how are you? I'm doing good. Thank you. Please kind of have where is, what do I do, directions, and let's say maybe some accommodation and some extra pleasantries. You get these 10 things on the go. You're going to instantly get smiles and appreciation for trying to learn a local language.

and speak to them and converse with them. And it's going to help you a long way in certain situations. If you have no wifi, you have no maps, don't know where to go, you need to ask for directions. You might have someone in a shop, on a stool, in a market. So get some directions on the go. When you approach a hostel or a hotel and the local is working there, hello, how are you? This is also great for restaurants because they rely on that human interaction for business and you're making an effort for them means that they'll make an effort for you.

And it's a great transaction either way. I remember going to Lebanon, Oman in the Middle East area and learned a bit of Arabic. And I'm going to chuck in their Turkey at the top for learning Turkish as well. They could not believe that I was saying, hello, how are you? An instant warmth, smiles, and a willingness to help you out and answer your question. You may not know the answer in their language. I'll come to that in a second, but at you're there ahead of someone who just only speaks English.

This is so key to traveling locally. Now, top tip I use here, get AI on the go, chat, GBT, Claude AI, whatever you want to use, put in, give me 10 senses that are most frequent to ask in a local language, then ask it to list underneath the replies that you're going to get because there's a slight stress when you ask a question and you don't understand the answer. So if you can ask the question, great, number one. Number two, you might know what the answer is going to be and you plan your reaction to that. You've got a three way conversation there for three senses and you're in.

This is so key to local travel. It's one of the biggest lessons I've learned and every country I go to around the world, I'll make sure I learn 10 sentences for each language. Get it done. Number five, off season is the best part of the year to travel. Yes, for a number of reasons. Number one, lower prices. Number two, less people. Number three, you don't annoy the locals as much because they're not too hot on people traveling in.

James Hammond (:

peak season. Number four, help the travel economy going all year round. Number five, you have a much more enjoyable trip. Number six, higher availability for activities, accommodation, flights, transport, et cetera. And I'll go finish with a lucky seven. Why do you want to be with whore to people? So for example, I only travel in the off season in Europe and North America.

basically the opposite of the school holidays. But do bear in mind in other parts of the world, in Asia and South America, you're going to have the rainy season to deal with. So the weather will dictate what parts of the year you can go. But right now in places like Barcelona, Venice, Dubrovnik, the locals are fed up with over tourism. And it doesn't mean they don't want you to travel there. It just mean they don't want hordes and hordes of tourists in those summer travel months or the school holidays. It's too much for them. But you go to Barcelona in February,

could be decent weather, way quieter. You'll have much better time. You don't want to be there when the hordes of tourists come from the cruise ships and clog up the place. You can see why they're fighting back a little bit. COVID made them realize what the city could be like in non-touristy season. It's a nice city. It's great to live in and it's manageable, should we say. But don't get me wrong, they do want tourists as part of their economy, but just make sure you share it out.

eled to Greece in December in:

in the off season. Thanks for listening to the first five points on this episode. I hope they mean something to you. Definitely means something to me. But before we crack on with the second half, please take a chance to rate and review this podcast. Five stars and a written review is absolutely awesome for winging it. It's free, takes two minutes and it really helps a podcast that you wouldn't believe. Second of all, if you want to support the podcast via some money, you can buy me a coffee for $5 if you head to the show notes.

James Hammond (:

the buy me a coffee link, hit that, buy me a coffee and I'll mention you on the next episode. And finally, if you can't do either of those, word of mouth is the best way to spread the podcast. Tell your friends to check out Wing and it. They can tune in with different types of episodes like immersive episodes, soda episodes like this, or the amazing guests I've had on the four and a half years of doing this podcast. Right. That's enough of me rambling. Let's get back into the second half of the episode.

And thanks for your help. I appreciate you listeners. You mean well to me. Let's go. Number six, nature is the real luxury. Yeah, this is not for everyone this one, but for me, I have found out that I do love city breaks. Don't get me wrong. I love it. But I've got a real appreciation for nature, but working for nature. So what I mean by this is I love a good hike. I'm a really bad hiker. I moan, I curse, I ache. I'm not that fit. It's just not the thing I'm good at.

But I love the end point. I love the guest house. I love the Dao Bat in Nepal. I love meeting locals on the trail, but I love the views. mean, imagine waking up at sunrise on Poon Hill in Nepal and you've got an 8,000 meter mountain there, the Annapurna. Incredible. Blue skies, bit chilly, but you've worked for it. That is four days of hiking. Like unbelievable. Whether that's a Cook Islands beach. Cook Islands is insane. Like the best beaches I've ever been to. I heart on about it.

every day in my mind. Amazing nature, Nepal with the mountains, incredible. But the Rockies here in Canada, the islands, like there's so much around the world that you can go and see and do with nature. I do think it's king and it should be a big part of your trip. And for me, I always bake it into every trip I go to because I know once I'm in nature and I've worked for it and I'm there amongst it, I feel better as a person. It makes me feel good about traveling, but also increases the respect for this world and how much we should look after it.

ke I did in Southeast Asia in:James Hammond (:

a little bit of WhatsApp going, maybe a of Instagram or Facebook, whatever. But on the whole, you'll never have that experience ever again, that same people at the same time, nowhere near. And you might not even see these people again, but you know in your mind you had the best time for two days. I know so many people I've met traveling that I've loved, I would love to meet them again, but life has just gotten in the way. But I accept that that moment in time and in history was an awesome time. And I struggle to accept it sometimes because I...

tried to chase those experiences. But for me, there's a beauty in that that is a finite time in history where we had the most amazing time. And maybe that's all that is supposed to happen. I have so many fond memories of travel and of the people I've met on the road. I do try to keep in contact. We all do, but life gets in the way. You're in different places around the world. And sometimes maybe that's it. But life is precious. Travel is precious. And these friendships are something you'll look back to in the future, maybe now and think, a great time we had.

Bittersweet, isn't it? But travel friendships are unique for a simple fact is, you're a foreign country, doing a foreign experience in a foreign land, foreign language. And that day or two is just the most wonderful experience. Number eight, budget travel teaches resilience. Now budget travel is not for everyone, but I've done a lot of that in the past, especially in my 20s into my early 30s. I'm probably a bit over the hump now, I'm more mid range, but I think that comes with age. But when you budget...

in your 20s and 30s. You realize how much more further your money can go on your trip. Oh, should I book that hotel? No, let's save a third of the cost and have an extended time in that place. Budget teaches you to make your money do more for you on your trip. That can extend your trip. It can give you more experiences or even make it just a bit more comfortable in those odd times that you need it. But it teaches you to budget your food, your daily costs, your accommodation, work out the range of budget. You have an amount of money saved here.

ewhere else. So what I did in:James Hammond (:

Went for six months and they're back in those days. It's cheap, isn't it? Looking back, six thousand pounds. Six months. That was three months in Southeast Asia, a month in New Zealand, two to three weeks in Fiji and however long the money lasted in Australia, which is about six weeks. I was desperate for a job. East Coast, met someone in Magnetic Island, gave me a number. Okay, better ring this number for a job. Got the job next day, flew down, start working. Instant. So speak to people.

Learn about what the best value is in the country. Don't go too cheap. Cheap is not a great word. Go for good value. And I promise you the budget going forward will help you in the long term for travel. So what I've learned for number nine is slow travel beats ticking boxes. If you can, this depends on a number of factors. Slow down, take your time, don't rush and really soak in and drink it in, in terms of the place that you're staying in. I know this can be difficult on pay time off. You've got two weeks.

t slow and take your time. In:

another four days, we had to force ourselves to leave, cross the border into Cambodia and carry on the trip round. But we had no real plan. We're kind of like, yeah, if we like a place, we'll stay for a few more days. If we don't, we'll move on. And that's a cool way of traveling if you can. Slow travel also means you get to delve into local culture. You can do free walking tours, meet local people, do more things and learn more things in that place. Fast travel, you're ticking things off as more hedonistic. It's maybe the travel for youngsters. Yeah.

I don't go against that. We've all done that in our early 20s. But as you go on into your late 20s and 30s, travel becomes more wholesome. You want to take your time, slow down, you're a bit more tired and you want to learn more about the local culture, people and place. And to finish on this going forward, I like the combination of doing my projects like the podcast and YouTube and doing travel at the same time. But I can't do both at the same time whilst doing fast travel. I to take a few days out, do my projects and do a few days of travel or exploring.

James Hammond (:

yin and yang, mix them up, see where you go. I think that is possibly the best way to do it. We come to the last one. A key point for number 10 is the world is a much kinder place and it's much more kinder than media will make it seem. Every place I go to has amazing, incredible people. They're to help you and from you teach you, help you out in times of crisis. I've actually said this on another video on this vlog.

But I cannot stress enough that the majority of the general people in this world will help you out and be nice to you and make sure nothing comes bad of you. It's so true. Every country I've traveled to, there's always great people. Don't get me wrong. There's the odd idiot that's everywhere. Can't avoid them on the whole. If you're traveling somewhere, you're going to meet some sensational people. To add to this, if you think about traveling to a country you don't know too much about, you're a bit nervous about, try it out anyway. I promise you, you'll have a great time.

And what's the worst that can happen? You probably learn something about yourself in the meantime. So for this point, get out there, meet local cultures, learn local customs, eat local food, and I promise you, it'd be the best thing you'll do in your life. That's my top 10 lessons I've learned so far my travels. It might change in the future as I do more travels. And for me, a lot more travels coming up, a lot more things to learn, a lot more things to see and do. And the only way to learn more is to travel more, be more present and live in.

the moment and the day. Let's go traveling. Catch ya. Thanks for tuning in to the podcast episode today. If you've been inspired by today's chat and want to book some travel, if you head to the show notes, you'll see some affiliate links below which helps support this podcast. You'll find Skyscanner to book your flight. You'll find Booking.com to book that accommodation. Want to stay in a super cool hostel? You'll see Hostel World down there too. You'll find Revolut to get your travel card sorted. Click the GIGSky link to get your eSIM ready for your trip.

And more importantly, you'll find safety wing insurance to get that travel insurance for your trip. There are many more to check out. So when you click that link and book your product, a small commission goes towards me and the Wigginit Travel Podcast. Thank you in advance and enjoy your travels.